5-Ethyl-3-(2-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812036872

. 2012 Sep 5;68(Pt 10):o2838. doi: 10.1107/S1600536812036872

5-Ethyl-3-(2-fluorophenylsulfonyl)-2-methyl-1-benzofuran

Hong Dae Choi ^a, Pil Ja Seo ^a, Uk Lee ^b,^*

PMCID: PMC3470199 PMID: 23125643

Abstract

In the title compound, C₁₇H₁₅FO₃S, the 2-fluorophenyl ring makes a dihedral angle of 89.12 (8)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₁₇H₁₅FO₃S
M _r = 318.35
Monoclinic,
a = 11.290 (2) Å
b = 16.171 (3) Å
c = 8.5612 (14) Å
β = 105.045 (11)°
V = 1509.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.38 × 0.30 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.545, T _max = 0.746
7108 measured reflections
3129 independent reflections
2676 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.105
S = 1.06
3129 reflections
201 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ▶), 1271 Friedel pairs
Flack parameter: −0.05 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036872/fj2589sup1.cif

e-68-o2838-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036872/fj2589Isup2.hkl

e-68-o2838-Isup2.hkl^{(153.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036872/fj2589Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C12–C17 2-fluorophenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3ⁱ	0.95	2.53	3.420 (3)	156
C16—H16⋯O2ⁱⁱ	0.95	2.49	3.121 (4)	124
C5—H5⋯Cg ⁱⁱⁱ	0.95	2.79	3.692 (3)	159

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al. , 2010) and 3-(3-fluorophenylsulfonyl) (Choi et al. , 2011) substituents, we report herein the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group C_c in spite of having no asymmetric C atoms.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 2-fluorophenyl ring and the mean plane of the benzofuran fragment is 89.12 (8)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C12-C17 2-fluorophenyl ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-ethyl-3-(2-fluorophenylsulfanyl)-2-methyl-1-benzofuran (315 mg, 1.1 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colorless solid [yield 72%, m.p. 410–411 K; R_f = 0.61 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.